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Leading the Unleadable

Leading the Unleadable

How to Manage Mavericks, Cynics, Divas, and Other Difficult People
by Alan Willett 2016 240 pages
3.50
100+ ratings
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Key Takeaways

1. Exceptional Leadership is a Choice to Embrace Trouble

The very essence of being a leader and how you lead is itself a choice.

Leadership is Active. Leadership isn't a passive role or a title; it's a conscious decision to confront challenges head-on. Many managers find themselves in leadership positions through promotions or necessity, but exceptional leaders actively choose to embrace the difficulties that come with the territory. This involves accepting that trouble is inevitable and viewing it as an opportunity for growth and positive change.

Embrace the Good. Exceptional leaders actively embrace the many good things that come with leadership. You are in the right place to have a positive influence on others. You will be able to accomplish bigger and better things than you could accomplish on your own. You will be able to grow your own skills and abilities as you work with others, and you will gain not just from your own experience but through other people’s experiences as you work with them.

Trouble is Inevitable. The greater the responsibilities of leadership, the greater the amount of trouble you must deal with. This is why leaders often reach the point at which they wake up one morning and simply think, “I don’t want to do this anymore.” They have reached a leadership crisis point. There is a way forward, though.

2. People-First Mindset: The Core of Exceptional Leadership

Leadership isn’t just making a series of decisions (choices) on a daily basis.

People are the Priority. Exceptional leaders understand that leadership is fundamentally about leading people, not just managing tasks or processes. This requires a shift in mindset from focusing solely on results to prioritizing the well-being and development of team members. It means recognizing that people are the driving force behind any successful project or organization.

Empathy and Understanding. Exceptional leaders approach difficult situations with empathy, seeking to understand the underlying reasons for troublesome behavior. This involves appreciating the diversity of perspectives and starting with the belief that everyone has good intentions. It's about recognizing that people are complex and their actions are often influenced by factors beyond the immediate work environment.

Growth and Development. Exceptional leaders are committed to helping their team members grow and develop, even when faced with challenging personalities or performance issues. This involves providing constructive feedback, offering support and resources, and creating a culture of continuous improvement. It's about seeing the potential in every individual and helping them reach their full potential.

3. Trouble Radar: Spotting Issues Before They Explode

The earlier you are aware of issues emerging the more likely you will prevent damage and achieve the excellence desired.

Situational Awareness. Developing a keen sense of situational awareness is crucial for spotting trouble early. This involves paying attention to subtle changes in team dynamics, project progress, and individual behavior. It's about being attuned to the environment and noticing when something feels "off."

Active Listening. Talking to people and, more importantly, listening to people is the most obvious way to spot trouble. This involves engaging in regular conversations with team members, asking open-ended questions, and actively listening to their concerns. It's about creating a safe space for people to share their thoughts and feelings without fear of judgment or reprisal.

Data Analysis. Looking beyond the first level of data is essential for identifying underlying issues. This involves digging deeper into project metrics, performance reports, and other data sources to uncover potential problems. It's about questioning assumptions, verifying information, and using data to inform decision-making.

4. Transform Troublesome Individuals with Empathy and Clarity

The exceptional leader will face the problem fearlessly, directly, and quickly with the skill to transform the difficult people into the tremendous, lifting up the individual, and energizing the whole team in the process.

Preparation is Key. Before confronting a troublesome individual, it's essential to prepare thoroughly. This involves understanding your own emotions, moving past negative judgments, and crafting a clear, concise message that focuses on specific behaviors and their impact. It's about approaching the situation with a calm, rational mindset and a genuine desire to help the individual improve.

Direct and Empathetic Action. Taking proper action involves meeting with the individual in a private setting, delivering your message with empathy and respect, and actively listening to their response. It's about creating a safe space for open communication and understanding. The goal is to understand the individual's perspective, set clear expectations, and collaborate on a plan for improvement.

Focus on the Positive. Throughout the process, it's important to focus on the individual's strengths and potential. This involves highlighting their past contributions, expressing confidence in their ability to improve, and emphasizing the positive impact their improvement will have on the team and the organization. It's about creating a vision of success and inspiring the individual to strive for it.

5. Follow-Through: Building Bridges to Lasting Change

Follow through is critical to ensure success.

Intentions are Not Enough. A single conversation is rarely enough to transform troublesome behavior. Follow-through is essential for building a bridge to lasting change. This involves creating a detailed plan, publicly committing to new behaviors, and coaching others on how to provide support and feedback.

Ongoing Support and Feedback. Providing ongoing support and feedback is crucial for reinforcing positive changes and addressing any setbacks. This involves regular check-ins, active listening, and constructive criticism. It's about creating a culture of continuous improvement where individuals feel supported in their efforts to grow and develop.

Celebrate Success. Recognizing and celebrating successes, both big and small, is essential for reinforcing positive behaviors and building momentum. This involves acknowledging the individual's efforts, highlighting their progress, and celebrating their achievements with the team and the organization. It's about creating a culture of appreciation and recognition where individuals feel valued for their contributions.

6. When to Cut Bait: Knowing When Improvement Isn't Possible

Your leadership obligation is to the group as a whole.

Group Over Individual. While exceptional leaders strive to help individuals improve, their primary obligation is to the group as a whole. This means that in some cases, it may be necessary to remove a troublesome individual from the team or organization if their behavior is consistently hindering progress and negatively impacting others.

Evaluation Criteria. Making the decision to remove someone is never easy, but it's important to have clear evaluation criteria. This includes assessing the individual's willingness and ability to improve, their impact on team morale and productivity, and the availability of alternative solutions. It's about making a rational, data-driven decision that is in the best interest of the group.

Compassionate Action. Even when removal is necessary, it's important to act with compassion and respect. This involves providing the individual with clear and honest feedback, offering support and resources for their transition, and ensuring that the process is handled fairly and ethically. It's about minimizing the negative impact on the individual while protecting the well-being of the group.

7. Preventative Leadership: Setting the Stage for Excellence

Prevention is better than cure.

Clear Expectations. Exceptional leaders proactively prevent trouble by setting clear expectations of excellence from the outset. This involves defining specific goals, outlining desired behaviors, and establishing clear consequences for deviations from expectations. It's about creating a shared understanding of what success looks like and how it will be achieved.

Culture of Accountability. Creating a culture of accountability is essential for preventing trouble. This involves holding individuals responsible for their actions, providing regular feedback, and addressing performance issues promptly and fairly. It's about creating an environment where everyone is expected to contribute their best and where poor performance is not tolerated.

Continuous Improvement. Exceptional leaders foster a culture of continuous improvement where individuals are encouraged to learn, grow, and develop. This involves providing training and development opportunities, encouraging experimentation and innovation, and celebrating successes. It's about creating an environment where everyone is striving to reach their full potential.

8. Compelling Goals: The Mountains That Unite Teams

There is a need for challenges as high as mountains.

Shared Purpose. Compelling goals provide a shared sense of purpose that unites teams and inspires them to overcome challenges. These goals should be ambitious, meaningful, and aligned with the organization's overall mission. It's about creating a vision of the future that everyone can rally behind.

Emotional Connection. Compelling goals evoke emotion and create a sense of excitement and passion. This involves using language that resonates with people's values, appealing to their sense of purpose, and creating a vision of the future that inspires them to take action. It's about tapping into the human desire to make a difference and contribute to something bigger than themselves.

Collaborative Ownership. Compelling goals are not imposed from above; they are co-created with the team. This involves engaging team members in the goal-setting process, soliciting their feedback, and empowering them to take ownership of the goals. It's about creating a sense of shared responsibility and commitment.

9. Culture of Excellence: Daily Reinforcement of Expectations

If those interactions are not congruent with what is written on the walls, the hallways will win.

Consistency is Key. A culture of excellence is not built overnight; it requires consistent reinforcement of expectations in daily interactions. This involves aligning words with actions, modeling desired behaviors, and providing regular feedback. It's about creating an environment where excellence is not just a goal, but a way of life.

Key Interactions. Exceptional leaders understand that the culture of an organization is shaped by a number of key interactions, including project kickoffs, review meetings, status updates, and reward and recognition programs. By consciously shaping these interactions, leaders can reinforce their expectations of excellence and create a positive feedback loop.

Continuous Monitoring. Exceptional leaders are constantly monitoring the culture of their organization, looking for signs of trouble and taking corrective action when necessary. This involves actively listening to team members, observing their behavior, and analyzing data to identify potential problems. It's about being proactive and addressing issues before they escalate.

10. Lead Thyself: The Foundation of All Leadership

To be able to best manage the mavericks, cynics, divas, and other difficult people and situations, we have to first change our frames of reference in how we think about them.

Self-Awareness. Exceptional leaders understand that the foundation of all leadership is self-leadership. This involves being aware of your own strengths and weaknesses, understanding your emotions, and managing your energy levels. It's about taking responsibility for your own growth and development.

Personal Sweet Spot. Exceptional leaders identify their leadership sweet spot, where their passion, competence, and values intersect. This involves understanding what energizes them, what they're good at, and what provides value to others. It's about aligning their work with their strengths and creating a fulfilling and impactful career.

Continuous Improvement. Exceptional leaders are committed to continuous improvement, both personally and professionally. This involves seeking feedback, learning from mistakes, and constantly striving to become better. It's about embracing a growth mindset and viewing challenges as opportunities for learning and development.

Last updated:

Review Summary

3.50 out of 5
Average of 100+ ratings from Goodreads and Amazon.

Leading the Unleadable receives mixed reviews, with an average rating of 3.50 out of 5. Some readers praise its practical leadership advice and real-world examples, particularly for those in the tech industry. Others find it too basic or lacking in specific strategies for difficult personalities. Many appreciate the book's focus on self-reflection and continuous improvement for leaders. However, some reviewers feel the title is misleading, as the content covers general leadership principles more than handling truly "unleadable" individuals.

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About the Author

Alan Willett is the president of Oxseeker, a consultancy specializing in leadership development and organizational culture change. His clients include major technology companies like Oracle and Microsoft, as well as government agencies such as NASA. Willett's expertise lies in helping organizations improve their leadership capabilities and transform their corporate cultures. As an author, he draws on his extensive experience working with managers across various industries to provide practical insights and strategies for effective leadership. His work focuses on helping leaders navigate challenging situations and manage difficult personalities within their teams, with a particular emphasis on the technology sector.

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